Dichloromethane → 2-Methoxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-one

HRID 51220Notes

Reaction equation

HRID 51220 reaction equation
[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:6][C:5](=S)[N:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15].C(Cl)Cl.[BH4-].C([O+](CC)CC)C.Cl.[CH3:34][O:35][NH2:36]>CO.C(N(CC)CC)C>[CH3:34][O:35][N:36]=[C:5]1[N:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3](=[O:15])[C:2]([CH3:1])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:6]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 120563925-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-oneHCID 88042375Triethyloxonium tetrahydroborate

Product 1

HCID 865884982-Methoxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-oneYield 41.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

5-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one (0.87 g) was mixed with a 1M methylene chloride solution of triethyloxonium tetrahydroborate (3 ml) at room temperature. The reaction mixture was stirred overnight at room temperature. Methoxyamine hydrochloride (0.25 g) and triethylamine (0.61 g) in methanol (10 ml) were then added at room temperature to the mixture. After 1 hr. the solvents were evaporated under reduced pressure. The residue was purified by column chromatography (chloroform) to yield 2-methoxyimino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-one (0.38 g) having a melting point of 133-134° C.

Workup

  1. waitAfter 1 hr
  2. customthe solvents were evaporated under reduced pressure
  3. customThe residue was purified by column chromatography (chloroform)

Sources & evidence

ORD record
ord-c8ccdc3170f04c43a91105c5b9977836
Source dataset
uspto-grants-2004_03
Patent number
US06713629B2

Reaction notes

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